It may have something to do with your own"comfort Zone". As you sail more you learn more. The more you sail the more chance of getting caught in a squall. Experience starts here, if this is your first squall then it will be a new experience, all the reading and videos that have been seen and played out in your head will start to kick in.
After the squall you can raise the experience bar a bit. Practicing to heave to, deploying the drogue, reefing, learningweather patterns all takes time and practice. Practice makes perfect and doing is the only way to get experience, so be prepared to get wet, have long shifts at the tiller/wheel earning these merits of personal experience.
Going longer, farther and preplotting on charts also add to experience and in the end you expand your " Comfort Zone".
Sailing is a learned skill and can only be done through trial and error, re-fitting your boat helps with mechanical, being a DIY again brings experience to that comfort zone.
Somewhere from the purchase to the sailing aspect you must just do it, start small, aim small and you will learn in small easy steps.
As you plan longer and farther passages, each and everytime you gain experience and skills your ability to make informed decisions becomes easier and more sound with a good knowledge base and a comfort zone appreciative and respective to this base you have acquired.
Bottom line from a long winded post is you really have to get out there and just do it.
Bill

The best thing that prepared me for sailing offshore was working on the water commercially for about 15 years. You didn't get to choose weather windows, who else was aboard or wait until everything was mechanically perfect. You went in all kinds of weather, whenever and wherever there was a $ to be made. I also was lucky to serve under a number of different skippers, some good, some bad, some drunk and some sober but they all taught me something.
Experience is a combination of the miles under your keel, the disasters you have survived and who you drew as shipmates and captains.
As you grow older, you not only become more risk averse but you can smell trouble coming and avoid it or if you get surprised, you are better equipped to deal with it and bring your ship and crew through the problem in one piece.
I don't believe there is a measurement of experience and knowledge to 'qualify' one for bluewater sailing (whatever that is).
We all operate on a combination of both and never stop adding to it IMO.
A lot of it has to do with what is your comfort zone and whether you are in or out of it.
The most important thing is to never look back back except to check your wake to tell you that you are still on a steady course. Just one opinion... cheers, Phil

__________________
“If you end up with a boring miserable life because you listened to your mom, your dad, your teacher, your priest, or some guy on television telling you how to do your ****, then you deserve it.” ― Frank Zappa

..I dont think we would be reading anything Black Oak has written had he been trying to learn to fly as opposed to sailing...Very very unforgiven to mistakes and ignorance,whereas you may make many many different mistakes learning to sail and live to tell the tell..You will not make but a few mistakes learning to fly before it kills you!..I have had people say things like" You have got to be crazy to fly" when in fact ,you had better have some good sense about you or learn to do something that is a lot easier ,like knitting socks...

Black Oak I re-read this and thought that I should explain myself a little better.. I did not mean to imply that what you have done was based on ignorance ,more like you are very brave for going at it like you did..Your story is really cool, regardless of how you gained your sealegs..Keep on Keeping on...

Flying is 3 demensions, sailing/driving etc. is 2 demensions, big difference. Often pilots with just a little experience think they are much better than they actually are and that makes them dangerous. It takes a lot of time to be able to fly well and many pilots never achieve what could be considered as a reasonable skill level. Of course that doesn't stop them from thinking otherwise.

Flying is 3 demensions, sailing/driving etc. is 2 demensions, big difference. Often pilots with just a little experience think they are much better than they actually are and that makes them dangerous. It takes a lot of time to be able to fly well and many pilots never achieve what could be considered as a reasonable skill level. Of course that doesn't stop them from thinking otherwise.

If sailing were only 2 dimensional, we wouldn't keep getting these stories about groundings.

I'm a private helicopter pilot, a mono racer, and a beach cat boy, and a wannabe cruising cat cruiser... i wonder what that says about me.
I often find sailling to be more complex than flying.. maybe thats because I am looking harder at the complexities.

I don't see any comparisons between sailing and flying , just because both have navigation common.

Flying today is a highly technical " skill" , equally its heavily regulated and in flight pilots have access to virtually continuous ground based aids and voice communications. Flying is a " taught skill", and its a primary skill, the pilot for example isn't expected to fix the aircraft.

Sailing is a set of skills, quite an extensive list , coupled with increasing experience to help to apply those skills.

Equally the sea is far tougher medium then the air. With significantly more things to hit or to get into trouble over.

Good sailing is a life long collection of skills and experience. Even then we make all sorts of errors

Dave

__________________Check out my new blog on smart boat technology, networking and gadgets for the connected sailor! - http://smartboats.tumblr.com

Flying today is a highly technical " skill" , equally its heavily regulated and in flight pilots have access to virtually continuous ground based aids and voice communications. Flying is a " taught skill", and its a primary skill, the pilot for example isn't expected to fix the aircraft.

I suppose you're talking about commercial or military piloting. Private piloting does demand a bit of versatility in skills, and there are no more ground-based or voice-based aids to a private pilot than are available to a sailor.

I've never known anyone trying to liveboard a small private-pilot type aircraft - that is one big difference.

Because when we go blue water first time we have nil, and yet, most of us make it to the other side.
Knowledge - welcome.

Why? : because bluewater implies situations where one will (possibly) be left to their own devices. Imagine your Iridium dies and there is no way you can call CG to ask which side is the starboard. Etc.

I think going sans experience and knowledge is still OK just the chances of getting into some sort of trouble are not worth it.

To sum up, to me, the prerequisites are: strong sailing skills and some amount of very sound knowledge.